This dissertation uses the history of political thought to shed light on the disconnect between the prominent place of judgments about the character in American democratic life, and the marginalized place of those judgments in contemporary democratic theory. By tracing the origins of that disconnect back into the history of political philosophy, and by locating an alternative approach to questions of character in the political and ethical writings of Aristotle, the dissertation brings out important connections between contemporary democratic theory and key developments in the history of ideas, and it recovers an ancient account of character that turns out still to be relevant to the dynamics of modern citizenship. The dissertation begins by showing how character is key to Aristotle‘s distinction between "correct" and "deviant" regimes in the Politics: not only are correct regimes distinguished by the character of those who rule, but the distinguishing feature of citizen-rulers in more correct regimes turns out to be their ability to appreciate what is excellent in the character of their fellow citizens. I then trace the decline of Aristotle‘s approach in the work of Machiavelli, Hobbes, Rousseau, and Kant, showing how Machiavelli‘s famously unsettling account of the relationship between moral goodness, political leadership, and popular government made its way into the foundations of later democratic theory. Finally, I return to Aristotle, showing how his treatment of philia or "friendship" in his ethical writings provides an important prelude to the ideas from the Politics we will already have considered. By taking into account both the high and often noble aspirations that inform considerations of character but also their potential to derail into disenchantment or dangerous ill-will, Aristotle‘s approach offers a theory capable of engaging directly with both the promise and the pitfalls of character judgments in democratic life. / Government